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Diastereoselective Synthesis of Cyclopentanoids: Applications to the Construction of the ABCD Tetracyclic Core of Retigeranic Acid A |
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| Authors: | Junlin Zhang Xiao Wang Shuang Li Dian Li Song Liu Prof Dr Yu Lan Dr Jianxian Gong Prof Dr Zhen Yang |
| Institution: | 1. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055 (P. R. China);2. School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030 (P. R. China);3. Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, and Beijing National Laboratory for Molecular Science (BNLMS), Peking‐Tsinghua Center for Life Sciences, Peking University, Beijing 100871 (P. R. China);4. Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003 (P. R. China) |
| Abstract: | A concise and efficient approach for the construction of the tetracyclic carbon skeleton of retigeranic acid A is described. The key transformations include a novel Rh‐catalyzed 3+2] cycloaddition of enyol to afford cyclopentanoid E , bearing two contiguous quaternary stereocenters at the bridgehead positions, and an intramolecular Pauson–Khand reaction to construct the advanced tetracyclic core structure of retigeranic acid A. |
| Keywords: | [3+2] cycloaddition natural products Pauson– Khand reaction quaternary stereocenters retigeranic acids |